| Division Three | |||
| 09/13/2008 | Upperthong | 3 - 2 | Grange Moor |
| 09/20/2008 | Grange Moor | 1 - 1 | Brook Motors |
| 09/27/2008 | Skelmanthorpe | 2 - 2 | Grange Moor |
| 10/04/2008 | Grange Moor | 4 - 1 | Dalton Crusaders |
| Sheffield Junior Challenge Cup Round One | |||
| 10/11/2008 | Grange Moor | 5 - 1 | Rotheram North |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Grange Moor | 4 - 1 | Fenay Bridge FC |
| 10/25/2008 | Linthwaite Athletic | 4 - 1 | Grange Moor |
| 11/01/2008 | Grange Moor | 0 - 4 | Scissett |
| Sheffield Junior Challenge Cup Round Three | |||
| 11/08/2008 | ISG Doncaster FC | 3 - 2 | Grange Moor |
| FA Challenge Cup Round Two | |||
| 11/15/2008 | Sovereign Sports (WL) | 0 - 4 | Grange Moor |
| 11/22/2008 | Grange Moor | 4 - 0 | Lindley AFC |
| 11/29/2008 | Grange Moor | 6 - 0 | Holmbridge |
| 12/06/2008 | Shelley | 0 - 5 | Grange Moor |
| FA Challenge Cup Round Three | |||
| 12/20/2008 | Netherton | 7 - 3 | Grange Moor |
| 01/03/2009 | Heyside FC | 2 - 3 | Grange Moor |
| 01/17/2009 | Grange Moor | 3 - 2 | H.V.Academicals |
| Groom Cup Round One | |||
| 01/24/2009 | Paddock Rangers | 1 - 3 | Grange Moor |
| 01/31/2009 | Grange Moor | P - P | Heyside FC |
| 02/21/2009 | Dalton Crusaders | 3 - 4 | Grange Moor |
| Groom Cup Round Two | |||
| 02/28/2009 | Brook Motors | 1 - 3 | Grange Moor |
| 03/07/2009 | Grange Moor | 4 - 2 | Linthwaite Athletic |
| 03/14/2009 | Scissett | 4 - 0 | Grange Moor |
| 03/21/2009 | Brook Motors | 1 - 4 | Grange Moor |
| Groom Cup Round Three Quarter Final | |||
| 03/28/2009 | Grange Moor | 3 - 1 | Hade Edge |
| 04/04/2009 | Y.M.C.A. | 1 - 1 | Grange Moor |
| 04/07/2009 | Grange Moor | 3 - 0 | Shelley |
| 04/11/2009 | Grange Moor | 0 - 1 | Upperthong |
| Groom Cup Semi Final | |||
| 04/13/2009 | Heyside FC | 1 - 0 | Grange Moor |
| 04/16/2009 | Grange Moor | 0 - 2 | Y.M.C.A. |
| 04/18/2009 | H.V.Academicals | 1 - 3 | Grange Moor |
| 04/21/2009 | Lindley AFC | 0 - 4 | Grange Moor |
| 04/23/2009 | Grange Moor | 0 - 4 | Skelmanthorpe |
| 04/25/2009 | Grange Moor | 0 - 2 | Paddock Rangers |
| 05/02/2009 | Paddock Rangers | 2 - 1 | Grange Moor |
| 05/05/2009 | Holmbridge | 6 - 4 | Grange Moor |